MOLECULAR CATALYSIS AND INTERACTIONS IN AQUEOUS SOLUTIONS

Abstract

Results of an investigation of some of the mechanisms leading to the eventual hydrolysis of certain phosphonate esters are presented. Studies were concerned in general with nucleophilic exchange reactions involving these esters, and more particularly with the replacement reactions of isopropyl p-nitrophenyl methyl phosphonate (1370) and with the hydrolytic rates of certain other derivatives. Kinetic studies of hydrolysis of isopropyl o-hydroxyphenyl methyl phosphonate show that this compound hydrolyzes by three kinetically different mechanisms: (1) water attack on the unionized molecule; (2) hydrolysis of the ionized molecule by probable intramolecular catalysis; and (3) hydroxyl attack on the innized molecule, with the subsequent formation of o-hydroxyphenyl methyl phosphonic acid and the elimination of the isopropyl group. Effects of various nuclear substituents on the rate of hydrolysis of the phenolate esters were also determined.

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Document Details

Document Type
Technical Report
Publication Date
Jan 08, 1964
Accession Number
AD0428687

Entities

People

  • T. Higuchi

Organizations

  • University of Wisconsin–Madison

Tags

Communities of Interest

  • Energy and Power Technologies

DTIC Thesaurus Topics

  • Amino Acids
  • Arrhenius Equation
  • Buffers (Chemistry)
  • Chemical Reactions
  • Chemical Synthesis
  • Chemistry
  • Heat Of Activation
  • Hydroxides
  • Organic Chemistry
  • Sodium Hydroxide

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry